- Accession Number
- Small Molecule
- Approved, Vet approved
An antibiotic produced by Streptomyces lincolnensis var. lincolnensis. It has been used in the treatment of staphylococcal, streptococcal, and Bacteroides fragilis infections.
- External IDs
- U-10,149 / U-10149
- Product Ingredients
Ingredient UNII CAS InChI Key Lincomycin hydrochloride GCW8Y9936L 859-18-7 POUMFISTNHIPTI-BOMBIWCESA-N Lincomycin hydrochloride monohydrate M6T05Z2B68 7179-49-9 LFZGYTBWUHCAKF-DCNJEFSFSA-N
- Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Lincocin Capsule 500 mg Oral Pfizer 1964-12-31 2006-08-02 Lincocin Injection, solution 300 mg/mL Intramuscular; Intravenous; Subconjunctival Pharmacia & Upjohn Inc 1964-12-29 Not applicable Lincocin Solution 300 mg Intramuscular; Intravenous Pfizer 1964-12-31 2016-05-06
- Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Lincomycin Injection, solution 300 mg/mL Intramuscular; Intravenous; Subconjunctival X Gen Pharmaceuticals, Inc. 2015-07-05 Not applicable Lincomycin Injection, solution 300 mg/mL Intramuscular; Intravenous; Subconjunctival X Gen Pharmaceuticals, Inc. 2015-07-05 Not applicable
- International/Other Brands
- Lincobect / Lincorex
- CAS number
- Average: 406.54
- Chemical Formula
- InChI Key
- IUPAC Name
- (2S,4R)-N-[(1R,2R)-2-hydroxy-1-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(methylsulfanyl)oxan-2-yl]propyl]-1-methyl-4-propylpyrrolidine-2-carboximidic acid
Lincomycin is an antibiotic used in the treatment of staphylococcal, streptococcal, and Bacteroides fragilis infections.
- Structured Indications
Lincomycin is a lincosamide antibiotic that comes from the yeast Streptomyces lincolnensis. Lincomycin has been shown to be active in vitro against the following microorganisms: Aerobic gram-positive cocci: Streptococcus pyogenes and Viridans group streptococci; Aerobic gram-positive bacilli: Corynebacterium diphtheriae; Anaerobic gram-positive non-sporeforming bacilli: Propionibacterium acnes; Anaerobic gram-positive sporeforming bacilli: Clostridium tetani and Clostridium perfringens.
- Mechanism of action
Lincomycin inhibits protein synthesis in susceptible bacteria by binding to the 50 S subunits of bacterial ribosomes and preventing peptide bond formation upon transcription. It is usually considered bacteriostatic, but may be bactericidal in high concentrations or when used against highly susceptible organisms.
Target Actions Organism A50S ribosomal protein L10inhibitor Shigella flexneri
Rapidly absorbed from the gastrointestinal tract following oral administration. Approximately 20 to 30% absorbed orally in fasting state; absorption decreased when taken with food.
- Volume of distribution
- Not Available
- Protein binding
Protein binding decreases with increased plasma concentrations. Range, 28 to 86% (average, 70 to 75%). Albumin is not thought to be the primary binding component.
Presumed hepatic, however metabolites have not been fully characterized.
- Route of elimination
Urinary excretion after this dose ranges from 1.8 to 24.8 percent (mean: 3 percent). Tissue level studies indicate that bile is an important route of excretion.
- Half life
The biological half-life after intramuscular or intravenous administration is 5.4 ± 1.0 hours. The serum half-life of lincomycin may be prolonged in patients with severe impairment of renal function compared to patients with normal renal function. In patients with abnormal hepatic function, serum half-life may be twofold longer than in patients with normal hepatic function.
- Not Available
- Not Available
- Affected organisms
- Enteric bacteria and other eubacteria
Pathway Category Lincomycin Action Pathway Drug action
- Pharmacogenomic Effects/ADRs
- Not Available
- Drug Interactions
Drug Interaction Drug group Alcuronium Lincomycin may increase the neuromuscular blocking activities of Alcuronium. Experimental Atracurium Lincomycin may increase the neuromuscular blocking activities of Atracurium. Approved, Experimental, Investigational Atracurium besylate Lincomycin may increase the neuromuscular blocking activities of Atracurium besylate. Approved BCG vaccine The therapeutic efficacy of BCG vaccine can be decreased when used in combination with Lincomycin. Investigational Cisatracurium Lincomycin may increase the neuromuscular blocking activities of Cisatracurium. Approved, Experimental Cisatracurium besylate Lincomycin may increase the neuromuscular blocking activities of Cisatracurium besylate. Approved Decamethonium Lincomycin may increase the neuromuscular blocking activities of Decamethonium. Approved Domoic Acid Lincomycin may increase the neuromuscular blocking activities of Domoic Acid. Experimental Doxacurium chloride Lincomycin may increase the neuromuscular blocking activities of Doxacurium chloride. Approved Doxofylline The serum concentration of Doxofylline can be increased when it is combined with Lincomycin. Approved, Investigational Erythromycin The therapeutic efficacy of Erythromycin can be decreased when used in combination with Lincomycin. Approved, Investigational, Vet Approved Gallamine Lincomycin may increase the neuromuscular blocking activities of Gallamine. Experimental Gallamine Triethiodide Lincomycin may increase the neuromuscular blocking activities of Gallamine Triethiodide. Approved Kaolin Kaolin can cause a decrease in the absorption of Lincomycin resulting in a reduced serum concentration and potentially a decrease in efficacy. Approved Mecamylamine Lincomycin may increase the neuromuscular blocking activities of Mecamylamine. Approved, Investigational Metocurine Lincomycin may increase the neuromuscular blocking activities of Metocurine. Approved Metocurine Iodide Lincomycin may increase the neuromuscular blocking activities of Metocurine Iodide. Approved, Withdrawn Mivacurium Lincomycin may increase the neuromuscular blocking activities of Mivacurium. Approved Neosaxitoxin Lincomycin may increase the neuromuscular blocking activities of Neosaxitoxin. Investigational Pancuronium Lincomycin may increase the neuromuscular blocking activities of Pancuronium. Approved Picosulfuric acid The therapeutic efficacy of Picosulfuric acid can be decreased when used in combination with Lincomycin. Approved Pipecuronium Lincomycin may increase the neuromuscular blocking activities of Pipecuronium. Approved Pyrantel Lincomycin may increase the neuromuscular blocking activities of Pyrantel. Approved, Vet Approved Rapacuronium Lincomycin may increase the neuromuscular blocking activities of Rapacuronium. Withdrawn Rocuronium Lincomycin may increase the neuromuscular blocking activities of Rocuronium. Approved Succinylcholine Lincomycin may increase the neuromuscular blocking activities of Succinylcholine. Approved Tubocurarine Lincomycin may increase the neuromuscular blocking activities of Tubocurarine. Approved Vecuronium Lincomycin may increase the neuromuscular blocking activities of Vecuronium. Approved
- Food Interactions
- Take on an empty stomach, food decreases absorption.
- Synthesis Reference
Alexander D. Argoudelis, David W. Stroman, "Process of producing lincomycin nucleotides." U.S. Patent US4464466, issued June, 1972.US4464466
- General References
- Not Available
- External Links
- ATC Codes
- J01FF02 — Lincomycin
- PDB Entries
- 4wh5 / 5hkv
- Clinical Trials
Phase Status Purpose Conditions Count 0 Recruiting Treatment Osteomyelitis 1 1 Completed Not Available Bacterial Infections 1 1 Completed Not Available Healthy Volunteers 1 1 Completed Other Healthy Male Chinese Volunteers 1 1 Completed Other Healthy Male Volunteers 1 1 Completed Treatment Healthy Volunteers 1 2 Completed Prevention Migraines 1 2 Completed Treatment Nonconvulsive Seizures 1 2 Not Yet Recruiting Treatment Glioma of Brain / Gliomas / Neoplasms, Brain 1 3 Active Not Recruiting Treatment Epilepsies 1 3 Completed Treatment Epilepsies 1 4 Active Not Recruiting Treatment Cellulitis 1 4 Completed Treatment Epilepsy, Localization Related 1 Not Available Completed Not Available Focal Epilepsy With and Without Secondary Generalization 1
- Not Available
- Dosage forms
Form Route Strength Capsule Oral 500 mg Solution Intramuscular; Intravenous 300 mg Injection, solution Intramuscular; Intravenous; Subconjunctival 300 mg/mL
Unit description Cost Unit Lincocin 300 mg/ml vial 7.79USD ml Lincomycin hcl powder 3.29USD gDrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
- Not Available
- Experimental Properties
Property Value Source logP 0.56 HANSCH,C ET AL. (1995)
- Predicted Properties
Property Value Source Water Solubility 3.02 mg/mL ALOGPS logP 0.34 ALOGPS logP -2.2 ChemAxon logS -2.1 ALOGPS pKa (Strongest Acidic) 3.24 ChemAxon pKa (Strongest Basic) 8.41 ChemAxon Physiological Charge 1 ChemAxon Hydrogen Acceptor Count 8 ChemAxon Hydrogen Donor Count 5 ChemAxon Polar Surface Area 125.98 Å2 ChemAxon Rotatable Bond Count 7 ChemAxon Refractivity 103.19 m3·mol-1 ChemAxon Polarizability 43.91 Å3 ChemAxon Number of Rings 2 ChemAxon Bioavailability 1 ChemAxon Rule of Five Yes ChemAxon Ghose Filter No ChemAxon Veber's Rule No ChemAxon MDDR-like Rule No ChemAxon
- Predicted ADMET features
Property Value Probability Human Intestinal Absorption + 0.5937 Blood Brain Barrier - 0.9659 Caco-2 permeable - 0.8957 P-glycoprotein substrate Substrate 0.7945 P-glycoprotein inhibitor I Non-inhibitor 0.6755 P-glycoprotein inhibitor II Non-inhibitor 0.5633 Renal organic cation transporter Non-inhibitor 0.8868 CYP450 2C9 substrate Non-substrate 0.8417 CYP450 2D6 substrate Non-substrate 0.8837 CYP450 3A4 substrate Substrate 0.6389 CYP450 1A2 substrate Non-inhibitor 0.9222 CYP450 2C9 inhibitor Non-inhibitor 0.907 CYP450 2D6 inhibitor Non-inhibitor 0.9269 CYP450 2C19 inhibitor Non-inhibitor 0.9203 CYP450 3A4 inhibitor Non-inhibitor 0.9342 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9563 Ames test Non AMES toxic 0.7696 Carcinogenicity Non-carcinogens 0.9482 Biodegradation Not ready biodegradable 0.9622 Rat acute toxicity 2.5777 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9847 hERG inhibition (predictor II) Non-inhibitor 0.7163
- Mass Spec (NIST)
- Download (7.07 KB)
- This compound belongs to the class of organic compounds known as proline and derivatives. These are compounds containing proline or a derivative thereof resulting from reaction of proline at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.
- Organic compounds
- Super Class
- Organic acids and derivatives
- Carboxylic acids and derivatives
- Sub Class
- Amino acids, peptides, and analogues
- Direct Parent
- Proline and derivatives
- Alternative Parents
- Alpha amino acid amides / Thioglycosides / Pyrrolidinecarboxamides / Monosaccharides / N-alkylpyrrolidines / Oxanes / Monothioacetals / Trialkylamines / Secondary carboxylic acid amides / Secondary alcoholsAzacyclic compounds / Sulfenyl compounds / Oxacyclic compounds / Polyols / Organic oxides / Carbonyl compounds / Hydrocarbon derivatives / Organopnictogen compounds show 8 more
- Proline or derivatives / Alpha-amino acid amide / Glycosyl compound / S-glycosyl compound / Pyrrolidine carboxylic acid or derivatives / Pyrrolidine-2-carboxamide / Monosaccharide / Oxane / N-alkylpyrrolidine / MonothioacetalPyrrolidine / Tertiary aliphatic amine / Tertiary amine / Secondary carboxylic acid amide / Secondary alcohol / Carboxamide group / Azacycle / Organoheterocyclic compound / Oxacycle / Sulfenyl compound / Polyol / Hydrocarbon derivative / Organosulfur compound / Organooxygen compound / Organonitrogen compound / Alcohol / Organopnictogen compound / Organic oxygen compound / Organic oxide / Carbonyl group / Amine / Organic nitrogen compound / Aliphatic heteromonocyclic compound show 23 more
- Molecular Framework
- Aliphatic heteromonocyclic compounds
- External Descriptors
- monocarboxylic acid amide, pyrrolidinecarboxamide, L-proline derivative, carbohydrate-containing antibiotic, S-glycosyl compound (CHEBI:6472)
- Shigella flexneri
- Pharmacological action
- General Function
- Structural constituent of ribosome
- Specific Function
- Protein L10 is also a translational repressor protein. It controls the translation of the rplJL-rpoBC operon by binding to its mRNA (By similarity).Forms part of the ribosomal stalk, playing a cent...
- Gene Name
- Uniprot ID
- Uniprot Name
- 50S ribosomal protein L10
- Molecular Weight
- 17711.38 Da
- Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]
- Odom OW, Hardesty B: Use of 50 S-binding antibiotics to characterize the ribosomal site to which peptidyl-tRNA is bound. J Biol Chem. 1992 Sep 25;267(27):19117-22. [PubMed:1527036]
- Champney WS, Tober CL: Specific inhibition of 50S ribosomal subunit formation in Staphylococcus aureus cells by 16-membered macrolide, lincosamide, and streptogramin B antibiotics. Curr Microbiol. 2000 Aug;41(2):126-35. [PubMed:10856379]
Drug created on August 29, 2007 15:12 / Updated on March 02, 2018 05:22